How many flights depart from Region of Ontario to Chicago on average per day?

102 flights are operational daily from Region of Ontario to Chicago as of September 2025. The most popular departure time for this route is 6:00a.m., with 46% of flights per day taking off at noon.

How many flights depart from Region of Ontario to Chicago on average per week?

718 flights are operational weekly from Region of Ontario to Chicago as of September 2025. The most popular departure day for this route is Thu, with 15% of flights per week taking off on this day.

How long does it take to fly to Chicago?

Flight times from Region of Ontario to Chicago vary, but if you’re flying out of Ottawa and flying into Chicago O'Hare Intl Airport (one of the most popular routes), then the duration is 2h 08m on average. Another popular route from Region of Ontario to Chicago is flying from Toronto to Chicago O'Hare Intl Airport, which will take roughly 6h 11m. Keep in mind that layovers or delays could extend your travel time.

What is the cheapest airline that flies from Ontario to Chicago?

WestJet, Porter Airlines, and Air Canada are the most popular carriers operating from Ontario to Chicago

Which airlines fly to Chicago?

Air Canada, United Airlines and Porter Airlines are the top three most popular airlines that fly to Chicago from Region of Ontario according to our data. Air Canada is the first choice among our users, with 62% of people opting to fly with this airline when travelling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

When did momondo last update prices for flights from Ontario to Chicago?

Prices for flights from Ontario to Chicago were last updated today.

How many operators does momondo search for flights from Ontario to Chicago?

There are 5 operators available for flights from Ontario to Chicago as of September 2025.

How old do you have to be to fly from Ontario to Chicago?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Ontario to Chicago.

What documentation or ID do you need to fly to Chicago?

The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

C$ 185 Cheap Flights from Ontario to Chicago in 2025/26

1 adult

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Find the cheapest flights from Ontario to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

6:30 a.m. - 6:38 p.m.YYZ-ORD

13h 08m1 stop

7:43 p.m. - 2:05 p.m.ORD-YYZ

17h 22m1 stop

C$ 296Multiple Airlines

Find Deal

qua, 15 out - qua, 22 out

4:00 p.m. - 3:49 p.m.YYZ-ORD

24h 49m1 stop

5:05 a.m. - 2:40 p.m.ORD-YYZ

8h 35m1 stop

C$ 299Multiple Airlines

Find Deal

dom, 19 out - sex, 31 out

6:20 a.m. - 10:30 a.m.YYZ-MDW

5h 10m1 stop

3:00 p.m. - 11:18 p.m.MDW-YYZ

7h 18m1 stop

C$ 332WestJet

Find Deal

sáb, 1 nov - sáb, 8 nov

8:00 a.m. - 4:43 p.m.YYZ-ORD

9h 43m1 stop

5:30 p.m. - 6:47 a.m.ORD-YYZ

12h 17m2 stops

C$ 335WestJet

Find Deal

sex, 17 out - dom, 19 out

6:15 p.m. - 8:00 p.m.YUL-ORD

2h 45mdirect

12:50 p.m. - 3:57 p.m.ORD-YUL

2h 07mdirect

C$ 336Air Canada

Find Deal

sáb, 1 nov - sáb, 8 nov

1:10 p.m. - 4:24 p.m.YUL-MDW

4h 14m1 stop

9:35 a.m. - 4:00 p.m.MDW-YUL

5h 25m1 stop

C$ 338Porter Airlines

Find Deal

sex, 17 out - qua, 22 out

1:10 p.m. - 4:24 p.m.YUL-MDW

4h 14m1 stop

5:20 p.m. - 10:15 p.m.MDW-YUL

3h 55m1 stop

C$ 339Porter Airlines

Find Deal

qua, 8 out - qua, 15 out

6:15 p.m. - 8:00 p.m.YUL-ORD

2h 45mdirect

3:55 p.m. - 9:52 p.m.ORD-YUL

4h 57m1 stop

C$ 353Air Canada

Find Deal

sáb, 1 nov - sáb, 8 nov

6:15 a.m. - 8:01 a.m.YUL-ORD

2h 46mdirect

7:11 a.m. - 10:40 a.m.ORD-YUL

2h 29mdirect

C$ 358United Airlines

Find Deal

qui, 16 out - sáb, 18 out

4:55 p.m. - 6:41 p.m.YUL-ORD

2h 46mdirect

7:11 a.m. - 10:40 a.m.ORD-YUL

2h 29mdirect

C$ 365United Airlines

Find Deal

qui, 9 out - dom, 12 out

Air Canada flights from Region of Ontario to Chicago

Our best Air Canada deals on Region of Ontario to Chicago flight tickets

Air Canada

1 Nov

YUL6:15 p.m.Montreal Pierre Elliott Trudeau Intl

2h 45m

ORD8:00 p.m.Chicago O'Hare Intl

8 Nov

ORD12:50 p.m.Chicago O'Hare Intl

2h 07m

YUL3:57 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 336

Find similar

Air Canada

1 Nov

YUL6:15 p.m.Montreal Pierre Elliott Trudeau Intl

2h 45m

ORD8:00 p.m.Chicago O'Hare Intl

8 Nov

ORD3:55 p.m.Chicago O'Hare Intl

4h 57m

1 stop

YUL9:52 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 353

Find similar

Air Canada

1 Nov

YUL8:50 a.m.Montreal Pierre Elliott Trudeau Intl

7h 20m

2 stops

ORD3:10 p.m.Chicago O'Hare Intl

8 Nov

ORD7:15 a.m.Chicago O'Hare Intl

2h 05m

YUL10:20 a.m.Montreal Pierre Elliott Trudeau Intl

C$ 360

Find similar

United Airlines flights from Region of Ontario to Chicago

Our best United Airlines deals on Region of Ontario to Chicago flight tickets

United Airlines

16 Oct

YUL6:15 a.m.Montreal Pierre Elliott Trudeau Intl

2h 46m

ORD8:01 a.m.Chicago O'Hare Intl

18 Oct

ORD7:11 a.m.Chicago O'Hare Intl

2h 29m

YUL10:40 a.m.Montreal Pierre Elliott Trudeau Intl

C$ 358

Find similar

United Airlines

9 Oct

YUL4:55 p.m.Montreal Pierre Elliott Trudeau Intl

2h 46m

ORD6:41 p.m.Chicago O'Hare Intl

12 Oct

ORD7:11 a.m.Chicago O'Hare Intl

2h 29m

YUL10:40 a.m.Montreal Pierre Elliott Trudeau Intl

C$ 365

Find similar

United Airlines

8 Oct

YUL6:15 a.m.Montreal Pierre Elliott Trudeau Intl

2h 46m

ORD8:01 a.m.Chicago O'Hare Intl

12 Oct

ORD7:11 a.m.Chicago O'Hare Intl

2h 29m

YUL10:40 a.m.Montreal Pierre Elliott Trudeau Intl

C$ 370

Find similar

Fly from

Fly to

Route

Depart

Return

Price

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

qua 15/10

6:30 a.m.-6:38 p.m.

1 stop13h 08m

Chicago O'Hare Intl

qua 22/10

7:43 p.m.-2:05 p.m.

1 stop17h 22m

C$ 296

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

dom 19/10

4:00 p.m.-3:49 p.m.

1 stop24h 49m

Chicago O'Hare Intl

sex 31/10

5:05 a.m.-2:40 p.m.

1 stop8h 35m

C$ 299

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

sáb 1/11

6:20 a.m.-10:30 a.m.

1 stop5h 10m

Chicago Midway

sáb 8/11

3:00 p.m.-11:18 p.m.

1 stop7h 18m

C$ 332

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

sex 17/10

8:00 a.m.-4:43 p.m.

1 stop9h 43m

Chicago O'Hare Intl

dom 19/10

5:30 p.m.-6:47 a.m.

2 stops12h 17m

C$ 335

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

sáb 1/11

6:15 p.m.-8:00 p.m.

Nonstop2h 45m

Chicago O'Hare Intl

sáb 8/11

12:50 p.m.-3:57 p.m.

Nonstop2h 07m

C$ 336

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

sex 17/10

1:10 p.m.-4:24 p.m.

1 stop4h 14m

Chicago Midway

qua 22/10

9:35 a.m.-4:00 p.m.

1 stop5h 25m

C$ 338

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

qua 8/10

1:10 p.m.-4:24 p.m.

1 stop4h 14m

Chicago Midway

qua 15/10

5:20 p.m.-10:15 p.m.

1 stop3h 55m

C$ 339

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

sáb 1/11

6:15 p.m.-8:00 p.m.

Nonstop2h 45m

Chicago O'Hare Intl

sáb 8/11

3:55 p.m.-9:52 p.m.

1 stop4h 57m

C$ 353

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

qui 16/10

6:15 a.m.-8:01 a.m.

Nonstop2h 46m

Chicago O'Hare Intl

sáb 18/10

7:11 a.m.-10:40 a.m.

Nonstop2h 29m

C$ 358

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

qui 9/10

4:55 p.m.-6:41 p.m.

Nonstop2h 46m

Chicago O'Hare Intl

dom 12/10

7:11 a.m.-10:40 a.m.

Nonstop2h 29m

C$ 365

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Region of Ontario to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Chicago?

The month of June is another great option to travel to Chicago, with average flight prices from Region of Ontario averaging around C$ 310.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as C$ 644. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Tuesday because tickets tend to average around C$ 1,151. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

What is the cheapest time of day to depart on your flight to Chicago?

In the evening is the cheapest time of day to fly from Region of Ontario to Chicago when you can find flight prices for as low as C$ 621. Flying to Chicago in the evening is an ideal time because this is during off-peak travel hours. In the afternoon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,161 per ticket.

What is the cheapest Ontario to Chicago flight route?

Fly from Toronto Island to Chicago Midway for the best Ontario - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Region of Ontario when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around C$ 402 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Region of Ontario for as low as C$ 298 on momondo.

What cabin class options are available on Ontario to Chicago flights?

There are 4 cabin classes available to choose from on Ontario to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Region of Ontario to Chicago flights?

No. A direct flight is the cheapest option for a flight between Region of Ontario to Chicago.

Cheap Region of Ontario to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Region of Ontario to Chicago

Best price found	C$ 211
Fastest flight time	1h 49m
Direct flights	Every day
Airports in Chicago	1 airport

The best one-way flight to Chicago from Region of Ontario in the past 72 hours is C$ 211. The best round-trip flight deal from Region of Ontario to Chicago found on momondo in the last 72 hours is C$ 240.

The fastest flight from Region of Ontario to Chicago takes 1h 49m

Direct flights go from Region of Ontario to Chicago every day.

There is 1 airport near Chicago: Chicago Midway (MDW)

Search flight deals

When did momondo last update prices for flights from Ontario to Chicago?
Prices for flights from Ontario to Chicago were last updated today.
How many operators does momondo search for flights from Ontario to Chicago?
There are 5 operators available for flights from Ontario to Chicago as of September 2025.
How old do you have to be to fly from Ontario to Chicago?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Ontario to Chicago.
What documentation or ID do you need to fly to Chicago?
The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Region of Ontario to Chicago?
Based on momondo bookings for flights between Region of Ontario and Chicago, the leading plane model is De Havilland (Bombardier) DHC-8-400 Dash 8Q, making up 19.39% of the total bookings. Other popular models include Embraer 175 (Enhanced Winglets) with 15.55%, Boeing 737-800 with 12.07%, and Embraer 175 with 7.98%.

Best airlines flying from Region of Ontario to Chicago

Compare and see reviews for airlines that fly from Region of Ontario to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Porter Airlines	PriceFrom C$ 196	Free Cancellation	Rating 7.9 365 reviews	Search Porter Airlines flights
Air Canada	PriceFrom C$ 263	Free Cancellation	Rating 7.1 10,000 reviews	Search Air Canada flights
American Airlines	PriceFrom C$ 267	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
United Airlines	PriceFrom C$ 278	Free Cancellation	Rating 7.4 8,926 reviews	Search United Airlines flights
WestJet	PriceFrom C$ 381	Free Cancellation	Rating 7.2 3,095 reviews	Search WestJet flights

Munster

Hammond

Merrillville

Why use momondo?

Why should I use momondo to find a flight deal from Ontario to Chicago?

Finding the right flight to Chicago from Ontario is quick and easy when you have a range of options in front of you, from reputable agents and recognizable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Ontario to Chicago with flexible booking policies on momondo?

Flights from Ontario to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Ontario to Chicago?

Once all potential Ontario to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Ontario to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Ontario and alert you when they change.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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dom 19/10

dom 26/10

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Cheap flights from Ontario to Chicago from C$ 185

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Ontario to Chicago departing on 19/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names, great deals

Big names, great deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Ontario to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last-minute flights

Cheap direct flights

Air Canada flights from Region of Ontario to Chicago

Our best Air Canada deals on Region of Ontario to Chicago flight tickets

United Airlines flights from Region of Ontario to Chicago

Our best United Airlines deals on Region of Ontario to Chicago flight tickets

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Use the filters below to find and compare flights from Ontario to Chicago that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Region of Ontario to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago?

The month of June is another great option to travel to Chicago, with average flight prices from Region of Ontario averaging around C$ 310.

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

What is the cheapest Ontario to Chicago flight route?

Fly from Toronto Island to Chicago Midway for the best Ontario - Chicago flight prices

How far in advance should I book a flight to Chicago?

What cabin class options are available on Ontario to Chicago flights?

There are 4 cabin classes available to choose from on Ontario to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Region of Ontario to Chicago flights?

No. A direct flight is the cheapest option for a flight between Region of Ontario to Chicago.

What is the cheapest airline that flies from Ontario to Chicago?

WestJet, Porter Airlines, and Air Canada are the most popular carriers operating from Ontario to Chicago

Which airlines fly to Chicago?

How many flights depart from Region of Ontario to Chicago on average per day?

102 flights are operational daily from Region of Ontario to Chicago as of September 2025. The most popular departure time for this route is 6:00a.m., with 46% of flights per day taking off at noon.

How many flights depart from Region of Ontario to Chicago on average per week?

718 flights are operational weekly from Region of Ontario to Chicago as of September 2025. The most popular departure day for this route is Thu, with 15% of flights per week taking off on this day.

How long does it take to fly to Chicago?

Cheap Region of Ontario to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Region of Ontario to Chicago

Best price found

Fastest flight time

Direct flights

Airports in Chicago

When did momondo last update prices for flights from Ontario to Chicago?

How many operators does momondo search for flights from Ontario to Chicago?

How old do you have to be to fly from Ontario to Chicago?

What documentation or ID do you need to fly to Chicago?

What is the most popular plane model from Region of Ontario to Chicago?

Best airlines flying from Region of Ontario to Chicago

Compare and see reviews for airlines that fly from Region of Ontario to Chicago with momondo

Travelling to a place near Chicago?

Why use momondo?

Why should I use momondo to find a flight deal from Ontario to Chicago?

Can I find flights from Ontario to Chicago with flexible booking policies on momondo?

How can momondo help me find flights from Ontario to Chicago?

I’m not ready to book a flight from Ontario to Chicago right now. Can momondo alert me if prices change?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago